


The Diary of an Evil Overlord

by HunnyCake



Category: Original Work
Genre: Crack, Fantasy, Humour, Mild Language, Multi, Unrequited Love
Language: English
Status: In-Progress
Published: 2016-02-24
Updated: 2016-06-11
Packaged: 2018-05-23 01:07:51
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 14
Words: 10,143
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6099856
Author URL: https://archiveofourown.org/users/HunnyCake/pseuds/HunnyCake
Summary: <blockquote class="userstuff">
              <p>Have you ever wondered what an Evil Overlord has to go through? Well here's a sneak peak into their world. Read as they have to deal with those so called hero's, behead people, and dealing with a crush who REFUSES TO RETURN YOUR FEELINGS BECAUSE YOU'RE APPARENTLY EVIL AND YOU KILLED THEIR WHOLE FAMILY WHICH MEANS THEY HATE YOU (He's just playing hard to get).</p>
            </blockquote>





	1. The New Evil Overlord

Dear Diary

 

Exciting news I have just become the new Evil Overlord. Yay me :) . But I guess it’s a bit sad that my father did have to die so I could takeover and I was the one to kill him in his bed. However he did kill Granddaddy to become Evil Overlord so I’m just carrying on the family tradition. (Note to self don’t have children and get new guards)  
My coronation tomorrow will be amazing. I have it all planned out. I’ve waited since I was little for this moment.  
First there will be a parade with elephants, peacocks and maybe a tiger thrown in for good measure. Then I’m going to parade myself through the capital city and the people will cheer for me in joy and fear. The crown will be placed upon my glorious head the blood of course will be washed off beforehand. I don’t need my father’s blood on me again, that would be Totes awkward LOL. I will take the royal sceptre and make my first royal decree.

My first royal decree will be to kill all my father’s old advisers I don’t need the old coots they never liked me anyway and I don’t want a coup on my hands my first day as Overlord that would just be embarrassing. Then I’ll appoint all my friends as advisers:  
• Megumi will advise me on the state of the people. She’s a great people person I love her forceful way she interacts with the peasants.  
• Pepper will advise me on the economics. She always was good at math.  
• Shilo will be there for comic relief  
• Sofia will run the Law enforcement she shall be the Head Executioner. I know she’ll accept she’s wanted this job since she was five. Kinda weird thing to want to be when you’re older in my opinion but hey who am I to judge.  
• Eleanor will take care of the rest (hopefully)

Then I’ll kill the customary 73 peasants to celebrate my coming to power then I’ll break out the alcohol and party the night away. At the party there will be the best music for I’ll let the minstrel out the dungeon for the night perhaps I’ll even let him have the mouldy bread as a treat never let it be said that I don’t take good care of my people. The chef will make the best feast EVER!!!! There will be all kinds of cake, pigs wrapped in bacon, most things wrapped in bacon, all of the ice-cream, candy floss and of course a party would not be complete with a chocolate fountain which is a literal fountain. If my requests are not met, well let’s say the mystery meat we give to the school children won’t be as mysterious as it was before.

As they say go big or go home.  
Can’t wait to tell you how the celebrations go tomorrow.

Yours truly

The new Evil Overlord


	2. Coronation Day

Dear Diary

The celebrations were fantabulous. When I was making my way through the town in my carriage pulled by my favorite pitch black horses called Downfall and Ruin, I didn’t think the crowd was cheering loud enough so I set the tiger on them and pointed the elephant in their direction to stomp on them. The crowd went absolutely wild.  
The people shed a few tears when the customary 73 peasants were killed but as I said its custom I had to do it (well I didn’t have to but come on what’s a coronation without any MURDER boring that’s what).

I took my place on the golden throne and everything felt just right like everything had just fallen into place it was beautiful. The crown was placed upon my head it fit as if it was made for me (well it kind of was). When the royal sceptre was placed in my hands I felt the power surge through me it was totally awesome.

I then made my first decree ever I’ll never forget it. I decreed all my father’s old advisers were to be executed immediately. The looks on their faces was priceless I wish I had a camera so I could relive it over and over again. Seeing their faces I gave my first evil maniacal laugh, father would have been so proud.

They even begged me to spare them (so naïve and pathetic). I don’t know why they think I would keep them alive they thought I was a dumb spoilt brat (spoilt definitely but dumb no way). I know more than they think I do. I know they thought they could control me they had the audacity to think they could manipulate me to do whatever they wanted. But they were so wrong. I’m the only one in control.

ME!

NOBODY BUT ME!

ME!

I HAVE COMPLETE CONTROL!!!

Then I assigned my close friends as my new advisers I know for certain they have my best interests at heart I grew up with them after all we all planned for the moment I would take over from my father we know what we’re doing.  
Sofia took great delight in killing the old advisers. There was tons of blood it went everywhere it was a great way to really get the party started.

Then we stuffed ourselves full of food, Cook really went above and beyond the call of duty (Note as a reward let Cook visit his family in the dungeons he’s really earnt it). Can’t say I regret eating that much food but it may come back and bite me tomorrow. OMG Pepper got drunk and she is a total party animal when she’s drunk, maybe I should get her to drink more often she’s always so serious it’s good to see her let go for a bit. Sofia also got drunk but that’s not really surprising so of course she challenged a lot of people to a fist fight and won (Note get stronger guards). Shilo was so hilarious she went round pranking some of the guests making them think I was going to kill them (of course I’m only going to kill the useless ones) the looks of horror were priceless. Megumi and Eleanor filmed it all I can’t wait to re-watch it.

Can’t wait to see what happens tomorrow when I get some actual Evil Overlord work done.

Yours Truly

The Official Evil Overlord


	3. Worst First Day Ever

**Summary for the Chapter:**

> This chapter contains some mild language but the Overlord has had a rough day so they can be excused.

**Notes for the Chapter:**

> Mild editing of chapter has been done but not much a minor detail has been added

Dear Diary

Today was my first proper day on the job as Evil Overlord. But I had a massive hangover from the Coronation party the night before really taking the fun out of everything. I felt like shit I still feel like shit.

I had to sit and listen to the people’s problems and my GOD they are so whiny (it just made my hangover worse). Seriously what do they have to complain about I haven’t burned their houses down or killed them (yet). So really they have nothing to complain about.

But apparently they want “better” working conditions and “food”. I did think about just killing them all, just to get them out of the way. But Megumi said we can’t kill the whole population because apparently we need them to work for us and just because I have a headache doesn’t mean I can throw a tantrum and destroy everything (I hate it when she’s right).

So I spent the day sat on the throne brooding (totally not sulking).

Also to add to the worst first day ever, somebody tried to KILL ME.

HOW RUDE. I have done nothing to make them want to kill me they could’ve at least waited until tomorrow but NO I can’t just have a nice first day. NO the peasants have to ruin EVERYTHING for me.

Luckily I dodged the arrow and Sofia apprehended the, would be assassin by shooting him in the leg with an arrow. (Note get better guards ASAP). He was taken to the dungeons for ~~torturing~~ , questioning I look forward to personally questioning him tomorrow.

You know the assassin was a really big disappointment. I was told that the heroes were always handsome and strong and to keep my guard up around them. But this poor excuse of an assassin was ugly as fuck and was taken down by an arrow to the knee really I was told heroes were harder to take down, they really are pathetic.

I can’t wait for tomorrow to question the pathetic assassin. But it’s not all bad cook made me a really nice breakfast as a thank you for letting him see his family. I like Cook he knows his place. Also I can spend some quality time with Sofia when we question the assassin.

Yours truly

An extremley PISSED Evil Overlord


	4. Best Day Ever

Dear Diary

Best day EVER I got to ~~torture~~ , question the assassin from yesterday. He cried like a baby (how pathetic) it made me feel all warm and fuzzy inside.

With help from Sofia we got the necessary information out of him with some gentle persuasion (using the stretching rack, the laser and some knives placed in strategic positions)

So basically what he told us, is that there’s this rebellion that’s been in the works for a while now. They wanted my father dead, but I killed him for them so really they have no business trying to kill me, I mean I did them a FAVOUR. The rebellion doesn’t want me to be a ruler they want a so called “democracy” like the kingdom of Jubilance.

That really stung, I have feelings too you know. I’m actually very good friends with the ruler of Jubilance. Surprisingly we get along quite well they understand that we have our way of ruling our people and they have theirs and as long as we don’t attack them or try and takeover their allies we can do whatever we like in our kingdom, they are so understanding. 

Apparently the Rebellion planned to attack yesterday but changed their minds because they wanted to see what kind of Leader I was. But this assassin didn’t get the memo apparently. So really this is his own entire fault and not the Rebellions. So if I act better than my father did I don’t have to worry about another assassination attempt.

Even so I’m going to up security tomorrow just in case (you can never be too careful with these so called heroes). Maybe I’ll put up an ad to recruit new, stronger guards and retrain my current ones they really are shit at their jobs. It’s no wonder I was able to kill my father so easily with the lack lustre security around here.

Seriously if the Rebellion, actually had any brain cells they could have murdered my father years ago and I’d be sat as most likely a mafia boss (I am EVIL after all) in a democracy by now. 

I’m going to have to get the blueprints for the castle and check where all the secret passages are and get someone in to make sure the vents aren’t big enough to crawl through. Also I’ll have to put in new secret passage ways but I’ll do that myself, I can’t have anybody finding the new passage ways on any blueprints. I’ll also put booby traps in them, in fact let’s just put booby traps throughout all the secret passage ways.

As they say go BIG or go home.

So I had a look on Evil Black Market Amazon and found everything I need. I’m having sent in two books one on DIY secret passage ways and DIY booby traps. I also ordered in a whole bunch of tools and materials so I can do it, maybe I’ll get Shilo to help out if she’s not busy and Eleanor the less people to know about it and the more trustworthy the better.

I’m having a very hard decision to make now, should I kill the assassin secretly so the Rebellion doesn’t find out I know about them or do I publicly execute him, decisions, decisions.

You know what I thought about it, I need to make an example out of him so I’ll publicly execute him tomorrow at midday in the middle of the city. That should be prime time to show the people I’m not to be crossed. Also if I just say he’s dying for an attempt on my life and I give no mention of the Rebellion maybe they’ll think I don’t know about them.

Can’t wait to tell you how the execution goes tomorrow. Hopefully my order from Evil Black Market Amazon will also arrive I can’t wait I’m positively buzzing.

Yours Truly

A very Excited Evil Overlord  


	5. Help Little Timmy's Stuck In The Vent

Dear Diary

Today was a really busy day, I am exhausted.

So first off I got the blueprints for the castle in and found where all the secret passages are Jesus Christ, there’s a lot of them. I’ll have to block up some just so I don’t get confused or I could convert some into new corridors with extra rooms. I’m going to have to ask mother (she’s the evil queen of Calamitous, the Evil Kingdom 5 days travel, from here) whether I could do that with secret passages she should know she’s been in the Evil Queen game now for over 15 years.

There is, a strategic advantage to renovating the secret passage ways, if a certain Rebellion only has the old version of the blueprints they won’t know that anything’s been changed. So imagine their surprise when they are met with brick walls and corridors patrolled by guards. With all this Rebellion business going on I might as well extend the dungeons as well.

We also got Little Timmy in to check whether the vents are big enough to crawl through. Turns out they aren’t big enough. I wonder if he’s still stuck there. I’ve just now shouted down the air vent asking if he’s okay I got a sob, back in reply I’m sure he’ll be fine.

Sofia showed me the new training regime for the guards soon they will be the most feared guards in all the Twelve Kingdoms. She is also is going to get some new spies in, she’s looking at offering the best graduates from ESU (Evil Spy University) a job to work for the kingdom hopefully nobody else will snatch them up before we do. Soon we will uncover all of the Rebellions secrets. Sofia also showed me the posters she’s had printed advertising for new guards they’re great. The posters have inviting bright colours with just a hint of malice hidden underneath I’ll be getting new guards in no time.

Pepper informed me today that I’m spending way too much, so for the next few days I’ll have to cut down spending. I asked if we could make budget cuts on anything that wasn’t me. After looking into the kingdoms finances we decided to cut the welfare budget. A necessary evil as I improve Law Enforcement to deal with this so called Rebellion.

The execution was by far the best part of the day I rode into the city on Ruin and sat on the throne of Judgement to watch the execution. I was dressed in my best clothes for the magnificent occasion I just love executions I get to wear my crown and hold my sceptre. Megumi won’t let me wear them around the castle because apparently I’ll just mess them up. I hate it when she’s right.

I kept two of my best guards next to me (by that I mean the only guards that appear to have brain cells) just in case the Rebellion decide they want to kill me again so I have not one but two human shields to use to defend myself. Sofia marched the assassin to the execution block the assassin was shaking with fear (how pathetic). A massive crowd gathered around to witness the execution. Sofia was dressed in the customary executioner gowns and was wielding a massive axe to chop off the assassins head. Sofia announced to the crowd the assassin’s crimes, they gasped in horror. See they understand that trying to kill someone on their first day as Overlord is just plain rude.

An interesting development occurred a young woman ran forward crying. Turns out she was the assassin’s sister. She threw herself at my feet and begged me to free her brother the crowd was completely silent. I paused for dramatic effect, of course I already knew what the answer was but I wanted to put on a good show for the crowd. “No” I simply replied she tried to hit me after that but the guards dragged her away for questioning before she could even touch me.

I waved my sceptre to give the go ahead to Sofia. She chopped off the assassins head it had a look of disbelief on its face when Sofia held the head up for all to see. I think I’ll have it put on a spike in the throne room I get the feeling it will really tie the place together (it’ll be great for the feng shui of the room). The crowd cheered at the assassin’s death (as they should), they then returned to their dull meaningless lives.

My order from Evil Black Market Amazon didn’t arrive today; god they are so unreliable I hope they know this will impact their review.

So it really was a busy day I’ll have to ~~torture~~ , question the assassins sister maybe she can tell me more about the Rebellion. Maybe I’ll get some new guards tomorrow that will be interesting. Hopefully my package will also arrive tomorrow or else I’ll be really pissed.

Yours Truly

A very tired Evil Overlord


	6. The Letter

Dear Diary

 Last night was absolutely HORENDOUS, Little Timmy would not stop crying (Jeez he’s only stuck in the vent not like it’s the dungeon it could be worse. He’s such a fruit loop). I sent my pet bat Todd, down the vent to get him to shut up but to my dismay it only made him scream. So long story short that is how Megumi found me with, some butter trying to pull Little Timmy out of the vent, at midnight. She did give me a judging look but then again I must have looked pretty crazy dressed in my blue PJ’s with bunny slippers trying to pull Little Timmy out while he was screaming bloody murder. However, after some persuasion she reluctantly helped me pull Little Timmy out of the vent. Little Timmy seemed a bit shaken but I’m sure he’ll get over it. I hope he doesn’t tell his mother (my sister) about this little incident.

But then again his mother did send him to me to toughen him up a bit. Unfortunately, I have not succeeded and he is still a wimp even more so now. So after we got him out I escorted him back to his room in the dungeon (he’ll get a proper room when he stops being a sissy) and put him to sleep. I felt kinda bad for scaring him so I told him the bedtime story about the beast in the dungeons that eats little children if they tell their parents they were trapped in any vents. Judging by the terrified look in his eyes he got the hint.

So today started off great I got to ~~torture~~ , question the assassins sister. Turns out her name is Ashley I nearly had her killed on the spot for having the same name as my least favourite sister. But you shall be pleased to know I restrained myself. I supervised her questioning no matter what form or ~~torture~~ , questioning technique we used, she denied knowledge of a Rebellion. She was very convincing. So it has been decided that we’ll keep her in the dungeons in solitary confinement, for continued questioning, if she does not break within the week then she’s telling the truth and we’ll let her go (possibly).

Then part way through the day my package from Evil Black Market Amazon arrived. So I told all the peasants to come back tomorrow with their useless problems (I’ll get Megumi to deal with them tomorrow, I’m sure she won’t mind).

For the remainder of the day I looked over the books and planned out the new blueprints. The castle will be thoroughly equipped to deal with anything the Rebellion throws at me. Oh yeah the assassins head was put on a spike in the throne room today and I was absolutely right it really did tie the whole place together.

I also got loads of applications for guards, Sofia is looking over them but I get the final say on who we hire. I tell you some of the applicants are sooo hot if they don’t pass the test for guards they can always, come work for me as servants of some sort. I can’t wait to watch them train of course that will only be to see how good they are at their jobs not because I want to see them working out or anything that would be absurd.

 A letter also arrived today; the messenger was from my mother’s kingdom of Calamitous. I wondered if one of my siblings had finally killed mother and usurped her throne (I really hoped Axel was the one to kill her).

No such luck she’s still alive (how unfortunate). Mother has written to me saying that she will be visiting me for mother’s day. You see mother does not request to visit she demands and what mother demands, mother gets. This is a disaster what if the Rebellion embarrasses me in front of mother when she visits, she’ll think I’ve failed as a ruler. I’ll lose my standing in her top five favourite children. I’ve kept my position as a healthy third because I moved away from Calamitous at an early age to someday usurp my father’s throne instead of usurping her throne (now I did not do this because I liked mother, it was just easier for me to kill father). Now she wants to come here when I want to start renovating and get new guards. She really has the worst possible timing (I bet she knew and did it on purpose).

Oh shit. If mother is coming here for mother’s day that means my siblings will also turn up for mother’s day, like mother’s day couldn’t get any worse.  Also to add to matters I don’t know what to get her. It needs to be something good if I want to get the good guillotine for my birthday.

I need to go now to get a good night’s rest so I can be totally focused on getting everything ready for mother’s arrival. Hopefully everything will turn out well if it doesn’t let’s just say this; if things don’t heads will roll (literally).

Yours Truly

Evil Overlord


	7. Love

Dear Diary

Unfortunately today I did not get to prepare anything for mother’s arrival. It’s not my fault that the applicants for guards, happened to be very distracting.

You see today was the physical assessments for all of the people that applied to be my new guards. Now I may be biased but **_damn_** they were **_fine_**. It totally, had nothing to do with the fact that it was mandatory, for them to do the assessment shirtless (I totally had nothing to do with that no matter what Megumi says). Obviously I had to make an appearance to provide morale for the new troops and make sure they were truly capable guards. In fact I stayed for a good part of training, until Megumi dragged me away to do some actual work and because I was apparently drooling. (She is such a killjoy).

So I was then forced to listen to the peasants complain it was so BORING. To be honest I don’t know what they were complaining about because I really was not listening to a word they said. You see if I tilted my head back a bit and turned my head thirty degrees to the left, I could just see out of the corner of my eye, the guards practicing in the courtyard. As the peasants complained I nodded along to what they said, so it would appear as if I actually cared. Megumi however, caught on and closed the curtains so I was no longer able to see the guards (cold hearted bitch).

For about an hour I listened to the peasant’s problems, apparently the mines are very unsafe to work in. Now I know for a fact that the mines are perfectly safe to work in, I sent Little Timmy down them last week and he came out just fine. I mean sure ever since he went down there his asthma has gotten worse but hey it’s not like he died, it could be worse.   

Then an interesting development happened with the Rebellion today. The Leader of the Rebellion graced me with his glorious presence. He walked into the throne room like he owned the place and started making the demands (so forceful and sexy I like it).

Now I didn’t really hear his demands because **_damn_** his muscles were very distracting. OMG his voice it was so deep and silky it was to **_die_** for. I could not help thinking how powerful we would be if we joined forces and our children would be so beautiful and just perfect in every way. Alas he left as quickly as he came, I was very disappointed.

Luckily Megumi was paying attention and slapped me out of whatever reverie the Leader of the Rebellion had put me in.

Apparently these were his demands:

  1. Free Ashley supposedly they are lovers. (Yet another reason for her to die. Besides why does he want her when he could have someone like me?).
  2. Stop torturing prisoners (not going to happen it’s the only way to get reliable information out of people)
  3. Give up power in favour of a democracy (HELL NO NEVER. Also it would most certainly show mother that I'm a weak ruler and I need that new guillotine for my birthday)



After, Megumi had informed me of this I ordered, a wanted poster to be made immediately. I want to have him in my dungeons if it’s the last thing I do.

I have a plan to make him realise how stupid this whole Rebellion thing is, when he has me as an Overlord. When he comes to his senses he shall realise how great I actually am. Obviously he will be punished for his disobedience but I shall not kill him. He is too handsome to be killed and I will keep him in the castle as my slave and slowly Stockholm syndrome will take place and he will fall hopelessly in love me (just like it did with mother and my third step-father).

Here is my 10 step plan to making him love me:

  1. Ashley will be executed ASAP. (I need to rid myself of any competition)
  2. When he tries to stop the execution he shall be arrested.
  3. He will be thrown into the smallest and dirtiest prison cell.
  4. I personally will beat him for his disobedience. (Avoiding his face, it would be a crime to tarnish his handsome face. Though a scar may make it even sexier.)
  5. Then when I feel he has been punished enough I will upgrade him to a nice dungeon cell like the one Little Timmy sleeps in.
  6. He shall be kept for a week talking to nobody but me as I routinely give him his food ration.
  7. He will then be integrated into servant life.
  8. When he is comfortable in his lowly position he will be upgraded to my personal slave.
  9. I will flirt with him constantly while we are alone.
  10. When he starts returning my affection I shall marry him and we shall live happily ever after just like in the fairy tales.



The plan is absolutely full proof.  

I can’t wait to put my plan into action. But first I have to get things ready for mother’s arrival on mother's day so tomorrow I shall, focus on getting Little Timmy to toughen up she will be so pleased with the progress he has made.

Yours Truly

Evil Overlord


	8. Little Timmy Is Trained

Dear Diary

Today I toughened Little Timmy up to prepare him for the family business, which as you know is oppressing the masses.

Since the vent incident he has developed a nervous stutter so that’s the first thing that had to go. You can’t have a villain with a stutter it’s just not threatening. Now a stutter is fine for a minion but not a villain. So to cure him of this stutter I tried to beat it out of him. However, this only seemed to make the stutter worse but electric shock therapy seemed to work a lot better. The shock therapy did give him a nervous tick but hey I’ve heard the crazy evil look is really in fashion right now.

I tried to improve his fighting ability so he could impress mother with it. So to see what level he was at I started him off with something easy to slay which was a lion. He could not even land a hit so before the lion could eat him I quickly got Little Timmy out of the cage (his mother would have my head on a stick if he got hurt). Seriously though when I asked him if he’d been taught how to fight a lion in school, he said “they don’t teach that type of thing”, I mean really the standard of education is really slipping nowadays. When I was his age I was not allowed to eat lunch until I had killed at least two lions and a shark. So consequently I had to go back to the basics. I have to say I’m very pleased with his progress he can now kill a small deer without hurting himself.  

I also taught him his proper ABC’s I could not believe he hadn’t learnt them. I mean really my sister did not teach her child his ABC’s that’s just bad parenting, she’s lucky I’m doing this for her. So after beating him whenever he went wrong he has now learnt his ABC’s. I mean they are so easy I don’t know how he went wrong. It’s so simple it goes like this:

 **A** is for **A** pocalypse

 **B** is for **B** rutality

 **C** is for **C** atastrophe

 **D** is for **D** umbass

 **E** is for **E** vil

 **F** is for **F** uneral

And so on you get the gist of it. I mean really, how he had not learnt that is beyond me, it was the very first thing I learnt when I went to school. Seriously what are they teaching nowadays?

I also taught Little Timmy the key trait that all villains need to be successful **SASS**. I’ve got to say he was a natural (a chip off the old chopping block). It’s a relief to know he has a knack for something evil I was starting to get worried he had more heroic traits. However, I will beat him if he sasses me.

Now Little Timmy was also very lucky today he learnt about the politics of being an Evil Overlord. I set out the map of the kingdom and said “everything the light touches will never be yours”. So he asked “what about that shadowy place over there” to which I replied “that will also never be yours”. But I did tell him when he usurps his own parent’s throne; he can be the Evil Overlord of their kingdom he got very excited when I said that. He asked me whether I’d help him usurp his mother’s throne when the time comes and I replied “fuck yes I hate your mother, she’s a right bitch”. To be honest I thought he would defend his mother but he agreed with me. You know I feel that today has caused me and Timmy to become closer; maybe I’ll build him his own room when I start renovating.

Also today there was trouble in a secret passage way because Shilo couldn’t tell whether the blueprints said that the secret passage to the dungeons had booby traps or not. So I sent Little Timmy down to check, he went very willingly (aww he trusts me bless his little cotton socks, what a mistake he’s making). Turns out there were booby traps but I was very proud of Timmy for dodging the flames and avoiding the poisoned darts.

I now think I have prepared Little Timmy properly for mothers visit. She’ll be so happy at my progress with him; hopefully she does not recommend me as a mentor to any of my other nieces or nephews. I run a kingdom not a day care.

Yours Truly

A very proud Evil Overlord


	9. Preperation

Dear Diary

Today, I helped Cook plan the meals for mother’s arrival. It will be very classy there will be caviar, Kobe beef, Fugu, Foie Gras, Lobster and Oysters. Which are all of mothers favourite foods she loves them because they cost a bloody fortune I swear I’ll be bankrupt by the end of mother’s visit. I have told Cook that though I do complain about my mother and say I wish her dead he is not to poison the food. I also told him if mother compliments his food he will be able to visit his family for a whole month in the dungeons and I may even consider freeing them (if that’s not incentive to do well I don’t know what is).

I also went down to the dungeons to visit the minstrel to request he learns mother’s favourite song so he can play it throughout her visit. He will be learning the national anthem of Calamitous” if he fails to do this I’ll cut off one of his hands (I still want him to play piano for me).

I’ve ordered dancers from the Kingdoms school of ballet to put on a piece to perform in mother’s honour. They have been told if mother criticises any of their dancing I’ll make sure they never work in theatre ever again and the only job they will be able to find will be as waiters and waitresses at the theatre just to rub their inadequacy in their faces.

The Royal Guard has been hired now (they are so hot); today they were all fitted for their new uniforms. I did stop by to see how everything was going with the fittings; the uniforms really show their best features (so many muscles). Unfortunately the guard’s physiques did not spark the same interest in me as the Leader of the Rebellion. None of the guards could compare to him I wonder if he’s been thinking of me as much as I have been thinking of him. Speaking of the Rebellion I hope he does not embarrass me in front of mother.

Little Timmy has progressed well in his training, the nervous twitch is still there but he can now slay a full grown deer so progress is being made slowly but surely. As they say slow and steady wins the race. Since spending some one on one time with Timmy a sense of camaraderie has developed between us mostly due to our mutual hatred of his mother, we have even started planning her death. Seeing Little Timmy’s progress I have decided to upgrade him to bigger cell instead in the dungeons. I posed this idea to him today and he actually was so pleased he hugged me I awkwardly patted his back in return, as we were in the throne room in front of peasants and I have a reputation to uphold as an Evil Overlord in front of my people. I have also given him a pony to ride on when we meet mother at the border of the kingdom luckily he knew how to ride a horse. I really, have been nice to Little Timmy recently I’m going to have to kill some innocent peasants just to feel evil again.

Today I planned the seating arrangement for the banquet when mother arrives; at least my siblings had the decency to tell if they were coming and if they were not. I swear if any of them go back on what they told me and turn up uninvited I will tell mother their deepest darkest secrets. I know what all of their secrets are that’s why almost none of them bother me. Unfortunately my least favourite siblings Ashley and Rylen will be visiting too so I shall have to restrain myself from killing them. Lord I beg of you please give me strength.

While I was part way through deciding whether I should seat my favourite brother Axel on my left or my right, a person in graduation robes walked into the throne room. They walked straight up and gave me their diploma I opened it suspiciously and found they had graduated from ESU. They asked if there was an opening for a spy, I liked their confidence so I gave them the job. I can’t remember their name I know it began with an F. I think it might have been Floyd or Felicity or possibly Barry. I’m really gonna have to find that out. I handed the new spy over to Sofia so she could assess the spy and hopefully send them out to spy Rebellion.

So today I was very productive. I am prepared for mother’s arrival, Little Timmy and I have a plan to kill my sister and I gained a new spy. Today was a good day.  

Yours Truly

A very Productive Evil Overlord


	10. Keeping Up With The Siblings

Dear Diary

Today was absolutely horrific.

You want to know why.

My numerous siblings and their offspring turned up today. I was expecting them to arrive but I had forgotten just how much I hated all of them.

I let Little Timmy show my other nieces and nephews around the castle. I told him that if one of them somehow “accidently” got stuck in a vent or “accidently” ran into a booby trap in a secret passage he’d get a high five and his bedtime is never. He giggled evilly (they grow up so fast) and ran off to give his cousins a tour.

My least favourite sister Ashley arrived late in the day, I was hoping she would have got mauled by a bear on the way over but no such luck. She immediately started criticising my décor apparently heads on spikes is so last season I replied with “what would you know about décor, you don’t even have your own castle or kingdom, you still live with mother. So sit down and stop complaining bitch”. The look of horror on her face was priceless she spent the rest of the day sulking but she continued looking around my castle disapprovingly. Also whenever I said something to my less annoying siblings she’d sigh and roll her eyes it was so annoying.

Rylen also arrived unfortunately he also brought his offspring with him; I was hoping they were staying with his ex-wife seeing as its mother’s day tomorrow but no such luck. His child Little Sharon is the most deceitful and adorable girl you’ll meet she makes my skin crawl. To my dismay she did not go on the castle tour with Timmy so she was safe. She stuck to her father like glue the entire day, kissing his ass at every opportunity, complimenting him with her sickeningly sweet voice. If I could cut her tongue off, I would. To be honest I can’t tell whether she truly loves her father or if she’s just giving him a false sense of security and any day now she’ll kill him. To be honest I’d like her more if she did kill him.

There was an upside to the day my favourite brother Axel arrived. He proceeded to spend the day pissing off Ashley and Rylen. He also shouted at Little Sharon and made her cry (oh how I love Axel). Axel also commented on how far Little Timmy’s has come along since the last time he visited and praised me by giving me a lollipop. I then showed him to the wine cellar and he was right at home. That is the reason we get along he knows the way to my heart is through sweets and I know the way to his heart is through alcohol. We also have a mutual love towards each other because we both hate Rylen and Ashley with a passion.

Little Timmy did get his high five in the end because Little Florence got stuck in a vent. The telling off her mother gave her was very comical she even cried (such a pansy). She did get out alright though, she now does not trust Timmy and keeps jumping whenever he approaches her or speaks (aww already striking fear into people’s hearts. I’m so proud). He also took them through a passage filled with booby traps they all survived and now his cousins are thoroughly scared of him. I whispered to him that now they are all afraid of him he can bend them to his will, I told him to try it out. So now Little Timmy is being waited on hand and foot by his cousins (he’ll be great leader when he grows up).

So Little Timmy had a good day.

Unfortunately for me, my siblings insisted on showing me photos and talking to me about their offspring. I merely nodded and ordered more wine if they expect me to listen to them and actually care I need to be somewhat buzzed to do so. My brother Bernard also decided that he’d talk to me about the benefits of the democracy in his kingdom this is the reason he is mothers least favourite child (he is such a fruit loop). My siblings also tried to make small talk with me all through the day it was all so dull I nearly died of boredom.

I tried to sneak off and join Axel in the wine cellar but Megumi stopped me and dragged me back to the throne room to have more “quality time” with my siblings (cold hearted bitch).

So today was so boring. Wish me luck tomorrow for mother’s arrival.

Yours Truly

Evil Overlord  


	11. Mother's Day

Dear Diary

Today was mother’s day. What joy it was to have mother visit. (Note the sarcasm in that sentence)

Mother was very pleased with the events I had planned for her visit. She especially loved the fear on the population’s faces as we rode up to my castle. She even complimented the heads on spikes causing me to give Ashley a smug grin she looked mortified at mothers comment.

Mother seemed vaguely impressed by the performance the dancers put on. She even complimented my minstrel on his soulful rendition of Calamitous’ national anthem (looks like he’s keeping his hands, this time).  

I personally think I got mother her best mother’s day present if I do say so myself. I let all my siblings give their presents first; after all I wanted to save the best till last. When mother turned to me and asked where my present was, I clapped my hands for dramatic affect summoning the guards to drag in my mother’s least favourite advisor who had been on the run since he was uncovered to be planning my mother’s death. I then handed mother a knife and said she could do to him anything she saw fit. Mother then, using calculated steps walked towards the advisor and punched him in the stomach and then slit his throat. Judging by the crazed smile she had on her face after the advisor fell to the ground in a pool of blood, she loved my present.

Then we ate the banquet I forgot just how much I love family dinners. I love it because it’s a chance to see mother insult my siblings it’s very enjoyable. Mother did not insult me which is a first and commented on how well Little Timmy has progressed I smiled proudly at that I’ve worked very hard with Little Timmy after all. However she turned to Rylen and said that Little Sharon would benefit from my training, I may have choked on my wine when she said that. There is no way in hell I am training Sharon to do anything I couldn’t take it, she’d probably kill me in my sleep and takeover my kingdom or she’d just annoy me so much that I stab myself in the eye in shear frustration.

During the feast my new spy Floyd? Felicity? I don’t know their name came up to me and whispered in my ear that the Leader of the Rebellion was outside demanding entrance to the castle. I quickly excused myself to deal with this distraction.

When I met with Leader of the Rebellion our conversation went a bit like this:

So I may have run out of the castle and not given him a chance to explain himself and said “Can you not. Can you not, for just one day take a break from this whole Rebellion thing for one day? My mother is here and I can’t have you embarrassing me. It’s mother’s day don’t you have a mother to be with”.

 He then glared at me and said “no your father killed her”

I was a little taken aback at how angry he sounded at that, so I said “well that’s my father’s fault not mine, stop taking your anger out on me for something he did. Besides don’t you have a Grandma or something?”

He then got very angry at that and shouted “YOU KILLED MY GRANDMA DURING YOUR CORONATION!”

So I got kinda angry at how angry he was at me and shouted back “WELL SHE WAS OLD SHE WAS PROBABLY GONNA DIE AT ANY MOMENT I DID HER A FAVOUR!”

He then said the sweetest thing before he stormed off “YOU ARE THE MOST VILE CREATURE AND I HOPE YOU BURN IN HELL”

To which I replied “Why thank you very much that’s the nicest thing anyone’s said to me today good day to you sir” I then proceeded to slam the castle door.

I think he likes me I think he really likes me. He complimented me on how evil I am it warmed my heart and made my tummy go all gooey. But I did feel very angry at him, I mean why can’t he understand that this dictatorship is for the best and why is he angry at me for my actions they were all called for. His Grandma died as part of the customary killing of the 73 peasants he should feel proud of that, it is a great honour to die for your Overlord. You know I bet he’s just doing all of this Rebellion stuff to get me to pay him more attention. This is all just an elaborate plot for him to be able to spend more time with me it’s very unconventional but imaginative nonetheless. Maybe I’ll flirt back a bit more during our next interaction that will be very interesting.

 When I returned to my seat at the table my mother asked where I had disappeared off to and I merely replied there was a situation that I had to handle but it’s all sorted now. She smiled and complimented me on my efficiency and turned to Ashley and asked why she couldn’t be more like me. Ashley looked so angry I may have added salt to the wound by then saying, “yeah Ashley why can’t you be like me” I swear that if we weren’t in front of mother at that moment she would have thrown a knife at my face. Axel laughed throughout this interaction and fell off his chair in the process. So then I laughed at him so hard I also fell off my chair it was very funny.

Then we sent mother home in her carriage so all my siblings and their offspring finally left my castle.

When they had all left I breathed a huge sigh of relief.

I then threw an arm over Little Timmy and guided him to the kitchen so we could eat the leftovers with cook. I may also be his favourite relative at the moment as I let him have a few glasses of wine. I then tucked Little Timmy into his bed in the dungeons and went to my own bed.

So today went very well. Mother liked my gift, my siblings left and the Leader of the Rebellion complimented me. I can’t wait for tomorrow.

Yours Truly

A very happy Evil Overlord  


	12. Captured

Dear Diary

You may be wondering why I am writing to you on some scratchy roll of toilet paper with some charcoal. Well the answer to that is I have been captured by the Rebellion and I am being held in a small cage in their hideout.

This has got to be by far, my SECOND WORST DAY EVER. Of course my FIRST WORST DAY ever was when I was ten and got lost in a cave with Ashley and Rylen (don’t ask how long story) which resulted in them trying to eat me because we couldn’t find any other form of meat. I still don’t see why they tried to kill me, when Ashley had way more meat on her than I did, seriously if we had killed her we could have lived off her for two weeks at least. Luckily for me as I ran away from them as fast as my little legs could carry me, I found the exit thus narrowly escaping death.

Anyway you are probably wondering how I was captured.

You see I was on my way about to execute Ashley who’s, the Leader of the Rebellions girlfriend, when I’m ambushed by the Rebellion and captured. They used a smoke screen so none of my guards could see them when they grabbed me I think they used chloroform on me because a rag was put over my mouth and nose and it smelt really weird, then I passed out and woke up in this cage.

You know for the supposed good guys I’m being kept in truly shoddy conditions. I mean seriously they could have given me better conditions my prison cells are practically five star rooms compared to this. I have a thin rag that I suppose is what passes as a blanket around here, I also have a bucket for a toilet, how undignified.

 I know the reason they’re doing this to me it’s obvious really.

The Leader of the Rebellion likes me, he really likes me that is obviously the reason why he captured me; he wanted to be able to see me every day. I mean sure this is a very unconventional way of going about it, but the Leader of the Rebellion is a pretty strange guy, I mean he’s fighting for a democracy how silly is that when he has me as an Overlord.

However my love for the Leader of the Rebellion is unwavering, my heart has suffered greatly because right now this very moment, I can see the Leader of the Rebellion kissing Ashley passionately. These wet patches on the paper, are not to be confused with tear stains for I am too strong to show such weakness, the wet patches are just from the leaks in the roof of my cage. But obviously he his only kissing her to make me jealous why else would he be with such a slut. Well this deserves punishment; I’ll give him the silent treatment that should show him.

I’m very sorry you have been torn Diary. A member of the Rebellion tried to take you away from me just now, to see what I was writing they are so rude around here, don’t they know this stuff is private. So obviously I had to punish them, I did this by screaming and punching them repeatedly in their face until they started bleeding profusely and let go.

I fear they may have gone for backup I’ll have to hide you. I’ll talk more tomorrow; hopefully I will not run out of toilet paper.

Yours Truly

Evil Overlord


	13. Still Captured

Dear Diary

I am regretfully, still being held by the Rebellion. The breakfast I was given this morning was atrocious, I’m not quite sure what it was supposed to resemble and quite frankly I don’t want to know. Oh how I miss Cook, when he served me breakfast it was bacon and eggs and sausages all in the shape of a face it was delicious nothing like this disgusting pile of rubbish they gave me, which was only suitable to feed to the dogs. Thinking of Cook and his fabulous cooking, I almost feel bad about blinding him in one eye, woops.

The Rebellion made some pitiful attempts at torturing me today. I mean they didn’t have any knives or stretching racks, such amateurs it’s like they’ve never tortured anyone before. However I gave them the silent treatment, they’re not getting any information out of me, and besides I’m too strong to give in to such weak willed attempts at torture.

I wonder whether Sofia is close to finding me, I hope she is I can’t spend one more day in this hell hole I’ll go crazy (well even more crazy than I am now).

Little Timmy must be so worried about me, without me he has no one to guide him through life. Oh how I miss Little Timmy, I miss hearing his cries of fear when I send him down secret passageways to check for booby traps, I miss his look of terror whenever I’m near and most of all I miss his cute little flinch whenever I walk past him.

Oh my god, they tried to turn the whole questioning around by being nice. How on earth, do they expect to get answers when they’re being nice to me what kind of logic is that? The Rebellion truly is stupid absolutely stupid they’ll never get results with all this goodness malarkey. They gave me this whole speech about how I’m a good person and that there’s good in me and that I don’t have to follow in the family business. Excuse me I don’t do my job for anyone but me, I have planned for years to get where I am now and I’m not going to throw it all away for the likes of some simple minded peasants with a sexy Leader.

They are fools if they think I can be, as the peasant’s call it “rehabilitated”.   

Right now the fools are sat around a big table discussing something they’re speaking too low for me to hear. Really if they want to keep what they’re talking about secret why hold me in the centre of their hideout where they keep all their plans. Wait unless this is in a basement somewhere, which would be very embarrassing, I mean not that high profile if you’re trying to make a nationwide Rebellion and your headquarters is a basement probably in one of their parent’s houses. I mean come on to have this much time on your hands, to hold an Overlord and plan a Rebellion you’ve obviously not got a job so they have no money meaning they still live with their parents. I’m such a genius deducing all of this.

The Leader of the Rebellion is talking now, it’s a shame I can’t hear him, what I wouldn’t give to be able to hear his sweet angel like voice. Being so far away from him is torture. However, since he’s turned away I’ve got a very nice view of his ass. Now Ashley’s started talking, lord give me strength, she is so annoying. She keeps looking over and glaring at me. How rude what did I ever do to her, well I did torture her but she was kept in much nicer conditions in my dungeon and got some nice meals. In comparison I’m worse off, so I don’t know why she thinks she has anything to complain about.

Sorry you were torn again that bitch Ashley tried to see what I was writing. God doesn’t she know this stuff is private, was she never taught any manners? So naturally I had to punish her, I did this by punching and pulling her hair, I must say I am proud of myself I was able to rip out a generous clump of her hair. The Leader of the Rebellion separated us and when he did, get this he touched me. The Leader of the Rebellion touched me my life is now complete, his touch was like magic, I’m in love, I am well and truly in love.

Mark my words the Leader of the Rebellion will love me and if he refuses he’ll have to face the consequences of his actions. I will have to put my ten step plan into play soon if I am to win his affections. But judging from our previous interactions he wants me. So I won’t have to try too hard. Just you wait Ashley soon the Leader of the Rebellion will be **_MINE_** all **_MINE_**.

However, until I can put my plan into action I will have to wait for rescue. But I can wait, I am a patient person I waited years to be Overlord, so I can certainly wait a few more days for rescue.

I shall write again soon, however I am now running out of toilet paper so it might be a while.

Yours Truly

Evil Overlord 


	14. Journal entry #1106

Journal entry #1106

Leader of the Rebellion here.

The Evil Overlord is still in their cell, unfortunately they still aren’t talking, and it’s very frustrating because all they do is sit in there muttering and writing on toilet paper. I don’t know maybe it’s an inbreeding thing, I won’t judge if it is.

Trouble in paradise again, Ashley is mad that I was late to dinner last night. Well excuse me if trying to liberate an entire kingdom got in the way of date night, Jesus women can be so annoying (but she is hot so y’know I can overlook it). I’m sure some chocolate and roses will make everything okay.

Maybe the chocolate will soften her up when I tell her I have a kid from a previous relationship.

So apparently, the one night stand I had with that girl Jenny in Journal entry #224 gave birth to my kid. But she was not just a random Jenny, NO; she was Princess Jennifer of Calamitous daughter of its Evil Queen.

I have tried looking for my kid personally I grew up without a father, he died in the War of the five Kingdoms and I don’t want my kid growing up without a loving father figure. I didn’t get a lot of answers from Jenny all she told me was my son, who she lovingly calls Little Timmy, was sent to a relative of hers to learn the family business. I’m afraid I might be too late to stop Timmy’s corruption, but I shall not give up, I will save my son if it is the last thing I do.

The Overlord is crying again, it’s quite sad really. The Overlord is always so full of themselves and aggressive but after a few days in a cell they’re a crying mess. It’s moments like these that make me wonder if the Overlord is evil at all. I mean they haven’t tried to escape at all and they’ve only acted out when someone tries to see what they’re writing.

Personally I think the Overlord just has a few screws loose I mean living with the previous Overlord would certainly mess you up for life he was brutal.

The Overlord is wailing out different names now, I don’t know who they are but they must mean something to the Overlord. The Overlord just cried Timmy’s name I tried to question them about it but the Overlord just cried harder and started muttering things that I couldn’t hear through all the crying.

I’ll have to question the Overlord when they aren’t so emotional; though that may be a bad idea since they still haven’t co-operated during any of the interrogations.

A terrifying thought has occurred to me; what if Jenny sent Timmy to the Overlord? I can’t even begin to imagine the torture he could have gone through. I’ll have to find Timmy soon before it’s too late.

Leader of the Rebellion over and out

**Notes for the Chapter:**

> Sorry I haven't updated in a while I've had exams and writers block, I'll try and update more now.


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